Jane's Stories

Jane was my co-worker, and from the first time we met, I knew she was special. She was older than me, but I was attracted to her. We would flirt a little here and there, but I was always in one relationship or another, so even though I thought she might have similar feelings, we never discussed them. About a year after we met, she started dating Thomas, and from the moment I met him, I knew he must be well hung, but I had no idea.

Thomas is a former professional basketball player. Nobody I had heard of before - he only played on a professional practice team for a few years, never played in any pro games. He was at least 6'-7", black, thin but muscular, and had hands that looked like they could palm a watermelon.

This story begins a few years later, when I was working late with Jane. We were wrapping up the plans for a large event the next day in her office. We were both rather tired, and after spending the whole day together, I had been reminded of what I saw in her several years earlier. As I stood next to her, I started looking at her more intently, and her hazel eyes locked with mine. Suddenly, she kissed me, and I kissed her back. After a moment, she broke away and said "I know you've wanted that for a long time."
"I have" I said, overwhelmed.

"I wanted it, too, for a while," she said. "Since I met Thomas, I haven't really thought about it. But tonight, he's away and I am really horny, so what do you say, would you like to fuck me?"

In disbelief I said "yes, god yes. I've wanted that for a long time."

"Good," she said and started taking her top off. Before I knew it, she was topless and on her knees, removing my belt.
"It's been a long time since I saw a white dick," she said as she pulled my now-hard cock from my boxers. "you're bigger than I expected."
"Thanks," I said, and without thinking added "I'm sure it's nothing compared to Thomas."

"Oh no," she said as she pulled her lips from my cock. "Thomas is easily twice your size. I can barely fit Thomas in my mouth," she added just as she deepthroated my entire cock. Her large breasts swayed back and forth, rubbing my thighs as she worked me over.

"Holy shit," I thought. "I knew he must be huge, but twice my size??" At the thought, my dick got even harder.

After a few moments with Jane taking me down her throat, she stood and removed her pants. Jane had a large ass, but it looked good, round and surprisingly firm for its size.

Jane looked at me and said "I felt you get harder when I talked about Thomas's massive cock, did you like hearing about it?"

"I guess I did," I said, not even knowing what I was saying. I was so swept up in what was happening I just said whatever came to mind. "But I don't understand, if he's so much larger, why don't you just fuck him tonight?" I said as I slid my cock into Jane's surprisingly tight pussy.

"He's with a friend of mine tonight- Alexis," Jane said "She hasn't been fucked for a while and told me she was feeling pent up. I leant her Thomas for the night. She is probably nearly passed out from cumming by now, and Thomas will be talking her into giving up her ass to him."

I was stunned. So much was going on it took all I had not to cum at that moment. Here I was, finally fucking a woman I had wanted for years, who had without a doubt the most fantastic pussy I had even felt, and all the while she was telling me about her massively endowed boyfriend fucking her best friend.

"You let him fuck your friend?" I said, in disbelief.

"Oh yes," she said. "It works out quite well. I know he won't leave me, as you've probably discovered, I have an exceptional pussy. I have learned to control my muscles in ways that make Thomas go nuts. I don't think I can do it to you - it requires a bit tighter grip and your dick isn't quite big enough. Thomas's, on the other hand, is big enough for the feeling to be quite intense. He loves what I do to him, and he always comes back."

It made sense. Jane's pussy did feel incredible, and I could only imagine what it must feel like to be bigger and inside her.

"It works well, because the one thing Thomas loves almost as much as my pussy is anal sex, something I refuse to give him," she said. "So this way, he gets to go have his anal fix with my friends. With his huge dick, they cum several times - more than they've ever cum in their lives - and they'll do anything he wants by the end of the night. While they're catching their breath, he convinces them to let him fuck their asses. They're so delirious as that point that a few smooth words and about a bottle of lube later, they are face down on the bed with the biggest dick they've ever seen halfway up their asses."

"They just give it up?" I asked. In my life, I had always had to work on girls for months to get them to even consider anal sex, and here was a guy they were with one night getting it.

"Like I said," Jane responded. "By the time he's worked on them for a few hours, they will do anything he wants. They are like putty in his hands. That's just another benefit for me - my friends get to spend one night having the most intense sexual experience of their lives, and then know that he is all mine. I find selfish enjoyment in their jealousy."

I was pumping away furiously at Jane's pussy, completely turned on by her description of Thomas's power over these women. Jane barely acted like I was in her. Her tone was matter-of-fact. After taking Thomas so often, no wonder, she could probably barely feel me.
"Little Kristen, my friend upstairs, she licked his asshole on command."

I couldn't believe it. I knew Kristen, and she was not the ass-licking type. She was short, but incredibly hot. Kristen's ass, like Jane's, was big, but hers sat up, perky, and bounced as she walked through the office. Kristen was not the type to be pushed around either, she was scrappy, and I had always imagined her to be dominant in any relationship. The thought of her succumbing to a command to lick a man's asshole was incredible.

"Thomas's cock seems like it's the size of my forearm," said Jane, bringing up an incredible mental image of the length and thickness of Thomas's massive cock. "So you can imagine how it looks next to Kristen. It's more like her lower leg!" said Jane. "Thomas said he could only fit the first 7 inches of his cock into her ass, there just wasn't any way of getting it all in. That's when he decided to have some fun with her, and had her lick his ass while she stroked his immense cock."

"Who else have you loaned him out to?" I asked.

"He's had so many of my friends I've kind of lost track," Jane said, nonchalantly as I continued to pound away. "Lisa, Denise, Lori, Ashley...He actually made Casey pass out from the intensity of her orgasm, can you believe that?"

Casey was known to have a rather promiscuous past, and the stories she had shared with the girls around the office made it seem like she had experienced more sex than the rest of the office combined. That such a well-sexed girl had actually been physically overcome by Thomas's prowess was surprising.

"He really brought his A game to that one," Jane said. "Casey said after the fifth orgasm she had, she started shaking with pleasure and the next thing she knew, Thomas was standing over her trying to wake her. She was afraid to do any more that night, so she sucked him the rest of the way off, swallowing about a gallon of cum from those enormous balls of his. He had been saving up for a week, like I said, he wanted to bring his A game to her. He has always had a thing for redheads."

Hearing Jane tell these stores was the hottest thing I had ever experienced, and her pussy still felt tight on my now throbbing cock.
"Here's one you might really like," Jane said with a somewhat evil smile. "About the time Thomas fucked the living shit out of Marie."

My heart leapt. Marie was my ex-girlfriend. She was a slightly-chubby blonde with great curves and a cute face. Marie and I had dated for a short while before she broke up with me. Until I felt Jane's, Marie's was the tightest pussy I had ever felt.

Jane could sense my surprise.

"Oh yes," she said. "I saw Marie at the bar one night while I was out with the girls. She asked me what it was like to be with a black guy - she was obviously drunk. I told her I didn't know about other black guys, so I don't know if the rumors are really true, but that Thomas's cock was the biggest I had ever heard of. When I told her about it, I could tell she wanted to try it, so I suggested that she do. Thomas went over to her apartment the next night, and tight little Marie squirted for the first time in her life."

I had never even made Marie cum, let alone squirt. She had told me about ex-boyfriends who she could cum with, but it never happened with me.

"She said she didn't know what was happening at first, just that something felt incredible and different. Of course, Thomas knew and pulled out to let her squirt onto the floor. Thomas said she went nuts, riding his dick in every position she could think of, experiencing her most powerful orgasms ever in each one. Finally, around 4 a.m. he came in her ass and she fell asleep sprawled across the bed.

This was too much for me and I came in the most violent orgasm I can remember.

"I'm sorry," I said, realizing that I should have pulled out.

"No problem," Jane replied. "I'm on the pill and this amount of cum is nothing compared to what I'm used to. Did you enjoy that?"

"Oh my god, yes." I said, still reeling from the amazing feel of Jane's pussy and the stories she was telling.

"Good, I wanted you to know what it felt like, and to let you know that this belongs to Thomas."

"Wow," I said. "He is a lucky guy, and apparently you are a lucky woman."

"Yeah, since I didn't even come close to cumming here, I'll go home and use my vibrator thinking of Thomas, but like I said, you're bigger than I expected...from what Marie told me."

"What?" I asked, not putting two and two together.

"Oh yeah, she said you were nothing in the dick department, and that I wouldn't even be able to feel you, no matter how tight I am," Jane replied. "I could feel you, kind of, so be glad about that. She was probably just still in shock from the fucking Thomas gave her."

"Well, I guess you can always expect that from ex-girlfriends, she was probably just bitter after we broke up and I moved on," I said, trying to comfort myself, even slightly.

"I doubt that," said Jane. "This was before you guys broke up. In fact, it was the night before you guys broke up. I mean, why do you think she broke up with you? She's been trying to find a dick like Thomas's for her own ever since."

Okay, thanks for the feedback. I realize I'm a little wordy, but that's just me. As for the comments about the main character needing to 'win' - that was another idea I had for the same situation. Here's how that might start out, if you're interested in a 'Jane' Reboot (hey, if Hollywood can do it with Superman, I can do it).
__________________________________
"oh my god," Jane said as she felt the growing bulge in my suit trousers. "How big is this fucking thing?"
"Would you like to find out?" I asked, certain of the answer.
"oh, god yes..." Jane said breathlessly, amazed at the mass she was holding, and which my pants were trying to contain.
...

Jane and I had worked together for two years, and during that time I had come to be quite attracted to her despite her being several years older. Jane and I were working late this night, when I decided to show her what she had given up when she started dating Thomas.

Thomas, her boyfriend of about a year, was a former professional athlete - tall and muscular. All of the girls around the office were jealous of the catch Jane had gotten herself. Because of his size, and the fact that he was black, the girls in the office all assumed he was enormously well-hung. Of course, Jane was pleased with the attention this gained her and her responses only encouraged the other girls' fantasies.

On this day, I got tired of hearing yet another girl at the office snicker when Thomas came to visit Jane, and whisper to her cubicle neighbor what I can only image was related to what they thought Thomas had swinging between his legs.

Once Jane and I were alone, I started talking to her in her office about the event we were planning the next day, but stopped mid-sentence and said "You know, Jane, I've actually got a little bit of a crush on you."
"I know," she said. "But I have Thomas, and I certainly don't want to give up a good thing like that."

"What does he have that I don't?" I asked, leading her.
"Well, for one thing he has some decent money, he's handsome and athletic, and...to tell you the truth, he's pretty 'big' if you know what I mean." she said. She then held her hands up as if to show me just how "big" Thomas was.

"You know, Jane, what they say about black guys is just a stereotype...some of us white guys are pretty 'big' too." I said.
"Uh-huh," she said, shrugging off my response. "Well, I've been with a couple of guys in my life, but none compare to Thomas."
"I would make you cum like you've never known you could." I said boldly as I took a step toward her, stopping about a foot away from where she sat.
Jane was clearly shocked at the statement.

"What?" she stammered. "I mean....what?"
"Jane, I have wanted to nail you for a year now, and I know you've been attracted to me too," I said, "I've heard what you've told the other girls around the office - that Thomas is hung like a bull and can fuck you all night. I can top that. Look for yourself, I'm getting hard just thinking about throwing you over this desk and proving it to you."

"Would you like to find out?" I asked, certain of the answer.
"oh, god yes..." Jane said breathlessly, amazed at the mass she holding, and which my pants were trying to contain.
I stood Jane up and removed her top and bra, exposing her large breasts. I kissed her and removed my now straining pants. My large cock sprang forward as she lowered my boxer briefs.

I pushed Jane's head down slightly and she immediately acquiesced to my will, kneeling to take my massive cock into her mouth.
Jane sucked the large, purple head of my cock into her mouth. She sucked and nibbled on the head of my cock for a moment before releasing it and looking up at me.
"You have a huge dick, you know that?" she said. "This thing is incredible. I can barely fit my mouth around it, and I am used to taking Thomas's cock pretty far!" She said in amazement.

"Wait till I am inside you," I said. "I want you to tell me just how much bigger I am than Thomas, and how my cock makes you feel."
Jane moaned as she rubbed her pussy through her pants. "Gladly," she said as she stood up and removed her belt, letting her pants drop to the floor. She wasn't wearing panties, which I found incredibly hot.
"I wanted to be ready to fuck Thomas as soon as I got in the door tonight, so I left the panties at home," she said. "But I think this is going to be much, much better."

Jane pushed the stack of papers on her desk to the side and sat on the edge of the desk. I moved toward her, holding my cock like a club in front of me. I moved the head of my cock to her now dripping wet pussy and began to push the tip in."

"Go slow," Jane said with a little wimper as my cockhead pushed into her. "Thomas is long, but not nearly as thick as you...that dick of yours is like nothing I've ever felt."
I worked several inches of my cock into Jane and she threw her head back, moaning and squealing as I fed more and more of my cock into her tight pussy."

"You're very tight," I said. "I thought for sure you'd be looser after all that cock Thomas's been giving you." I smirked as I added the last part, knowing that she was not used to anything like this.
"Oh god, no," Jane said. "You are really stretching me out, and if you put that whole thing in me you will be reaching parts of me Thomas hasn't even come close to."

"Tell me..." I said.
"You're fucking huge. You're fucking huge!" Jane screamed as I pushed harder into her. "God! I am going to cum. Holy shit I am going to cum."
I smiled and moved my cock back and forth inside her, working the head of my cock against the walls of her pussy. I felt her grip get tighter on my dick and her hands slammed down, grabbing the edge of the desk.
"I'M CUMMING," she screamed. With that, her body started convulsing and I saw the muscles in her arms and legs flexing uncontrollably. Her entire body turned two shades redder as she trembled.

"How was that?" I said, slowly pumping in and out of her, letting her catch her breath.
"Incredible. The best," she said. "I have never cum like that, so quickly, and so hard. Even with my vibrator I can't get off like that."
"Good, we are only beginning..." I said as I rammed my cock into her.

Honestly, and I am not into humiliation in any real way, the first story was hotter. The buildup was slower and the content felt like it had more gravity; I would agree that a better option would be to make a sequel and have him transform somehow, getting revenge.